Third Wheel My ASS
by JennaIsHungry
Summary: AU High school where Dean and Castiel have been dating for a few months and although Sam was all for it at the beginning, he's starting to feel like he can't hang out with his brother without being a third wheel.
1. Chapter 1

The seconds on the clock tick by at the speed of molasses Sam thought. He was drumming his fingers on his desk and waiting impatiently for the ringing of the school bell to pierce the sound of his teacher's geometry notes.

Just as Sam was slipping into another day dream the blaring alarm rang and everyone got out of their seats and started to pack. It was Friday and you could hear weekend plans being made around the room. However, Sam was as quiet as a mouse. His desk was in the back of the class so he didn't usually talk to anyone. He didn't see the use of it. All he wanted was to go home and read while Dean makes burgers. He packed his things and headed straight for the door. Just before he passed the front row of desks right by the exit, he heard his name amongst the chatter.

"Sam! Sam wait!" It was a girl with blonde hair and probably the most enticing mix of blue and grey eyes. A few seconds passed before Sam realized that this beautiful girl standing in front of him was trying to actually talk with him.

"Uhm, hi. It's.. Jessica, right?" Sam hadn't gotten too familiar with his classmate's names but this girl raised her hand a lot and was always right. Sam subconsciously remembered her name ever since her first correct answer. "Can I help you with something or do anything for you or.. Uhhm," What would Dean do Sam thought, "what's up?"

"I was just wondering if maybe you wanted to grab a bite to eat sometime, maybe?" Her words came across as confident and fluid until a slight pause before the word "maybe" as if she finally realized what her mouth was saying. "No, no, wait. That sounded weird. Let me try again," she said while looking down and smiling. Sam noticed her blush slightly, but didn't say anything about it.

He laughed, "No, no. Not at all. Oh uhm I meant it didn't sound weird at all. Not that I was saying no to going out with you. Uhm, I meant, going out to eat.. with you." He was rambling like an idiot. He could hear Dean's voice in his subconscious telling him to slow it down and take a breath. "Do you have a cell phone? We can arrange something." Good. That was calm and cool.

Jessica's eyes lit up and she smiled while watching Sam pull out a pen from his backpack. She recited her number and the pen scribbled away on his palm. "I'll wait for your call.. Or text. Whatever you feel like," Jessica said nervously. She felt a weight in her stomach and the back of her neck getting warm.

"Yeah, I will. Alright well, see you soon, Jessica." Sam flashed a smile.

"By the way, you can call me Jess, if you want."

"Jess." With one last wave Sam finally headed out the door. His eyes were fixed on the tiled floor as he walked down the hall and recited the entire conversation in his head. Did that really just happen?

Suddenly, he took one step too many and smashed directly into someone's back. A junior. Sam's seen him around before. Spiked hair, ear pierced. He didn't know his name, and still didn't want to find out. Sam wasn't that big (yet) and definitely couldn't do enough to hurt the guy, but there was enough force to push the heavier boy off his balance for a second.

"I'm sorry. I didn't see you there." With that, Sam attempted to walk around him and go on his way.

"You think you can just walk away after shoving me, kid?" He caught Sam by the back of his shirt and yanked him around so that they were face to face. "You've got some nerve for a freshman."

"Look, I said I was sorry. I didn't mean to run into you."

"Yeah yeah save it, tiny. I'm sure my fist doesn't mean to run your jaw either." Sam really wasn't afraid. Dean's been training him in his self defense and Sam knew what to expect.

The taller, stalkier boy raised his fist near his ear. Sam was ready to deflect. The fist started to swing towards Sam's face. With perfect timing and placement, Sam's left forearm caught the punch by the wrist and forced it towards Sam's left side. Without a second to spare, Sam's right fist made a blow to the junior's ribcage. Seeing that his attacker was stunned and unable to retaliate, he made a run for it.

He flew through the crowds of people and burst out the front doors.

"Hey Sammy, where've you been? You're usually the first one out here!" It was Dean, casually sitting at the bottom of the stairs facing the parking lot. Castiel was sitting to his left and they were holding hands. Sam usually took this opportunity to say something to embarrass Dean in front of his boyfriend but now wasn't a good time.

"Hi Dean. Hi Cas. Let's get to the impala now!" Sam started down the steps and jumped the last five. "I'm not kidding lets go!"

The two seniors had confused looks on their faces but followed Sam to the car anyways. Sam had already buckled in his usual shotgun seat as the two older boys got in. They pulled out to the street and Sam could finally breathe again.

"Alright, Sammy now that we've sprung your getaway can you tell us what's going on?"

Sam finally caught his breathe and began to explain the bully and bruising his ribs.

"Sam, you could have gotten hurt," Dean finally said after hearing the whole story, "you know how to get out of someone holding the back of your shirt. Why didn't you get loose and book it?"

"But I didn't get hurt Dean! And I did what you said. I did run. Just after I swung at him. But then I ran right away!"

"You still could have gotten hurt." Dean's voice was authoritative and concerned. His eyebrows scrunched together at the thought of some jackass with a piercing taking a swing at his little brother.

Sam was sitting back in his seat and twiddling with his fingers in his lap. He didn't say anything more. He looked ashamed, as if what he did was wrong and he let Dean down.

Dean looked over to the passenger seat and knew he had to cheer the kid up some how. "You punch hard? Thumb on the outside like I showed you?"

The edge of Sam's mouth started to curl into a smile. "Open fist and upwards to the ribs. Just like you taught me."

They were both smiling now. "And how'd you stop the punch?"

"Deflected by the wrist outwards to leave him with his bad arm to protect his weak side," Sam cheered. His eyes were bright and the entire car's mood lightened up.

"That's by brother!" Dean raised his hand for a high five which Sam gladly met.

Castiel, who has been quietly sitting in the back seat finally piped in, "Sam you should be proud of your abilities to defend yourself at the age of fourteen. It is quite impressive."

"Thanks, Cas. Maybe I'll teach you sometime."

"No no no. Nuh-uh. Cas, you're not gonna be fighting anyone."

"Why Dean? What if I need to defend myself?" Castiel argued.

"Then I'll be there to beat the snot out of whoever is trying to lay a finger on you."

Castiel blushed in the back seat. "That's sweet, Dean

but-"

"No buts. Anyone who even tries to hurt you is dead meat. And you," Dean turned his attention to his brother, "if this guy ever gives you trouble, call me up and I'll be there. Alright?"

"Alright," Sam replied obediently.

They pulled into the parking lot of the apartment complex and headed up to the third floor. Sam plopped down in his favorite arm chair and Dean and Cas took the couch.

"Oh! I almost forgot!" Sam beamed in the middle of a shark documentary playing on TV. He displayed his palm to the couple on the couch. When they made out the scribbles they both cheered.

"You got a girl's number? Wait wait, you beat up a junior AND got a chicks number in one day?" Dean asked with disbelief.

"Sounds a lot like someone I used to know," teased Castiel while looking at Dean.

"Shut up. That was a long time ago." Dean said defensively.

"That's true. I haven't been sweeping up piles of paper with random seven digits off the floor for a while now." Sam joked. Sam and Castiel laughed and Dean rolled his eyes.

"Yeah yeah. But that was before you Cas." Dean smiled at Castiel's blushing cheeks.

Sam got up from his chair and made a fake barfing noise at the two lovebirds on the couch. Dean hit his brother's shoulder as he passed by. "Go call up that girl and plan something for the weekend. Go get her, tiger."


	2. Chapter 2

The afternoon went on as expected. Cas stayed for dinner like he's been doing for the past couple months. Dean made burgers, the best in the world in Sam's opinion. The three of them were crowded around the table devouring they're freshly grilled burgers while the TV played in the background.

"Hey Sammy, you wanna head out and shoot some targets tomorrow?"

"Yeah sure! We haven't got the guns out since last Christmas." Sam loved target practice with Dean. They had a competition every Christmas to see who could hit the most beer bottles. Sam hadn't won yet, but he was determined. He was already rehearsing the proper loading and unloading process of the shotgun in his head when Dean's voice sounded again unexpectedly.

"Wanna come along Cas?" Dean offered in a generous tone. Both his boyfriend and his brother responded with identical surprised expressions.

"Really? Are you sure? I wouldn't want to intru-"

"Yes of course you can come!" exclaimed Dean excitedly.

"We'll if it's okay with the both of you," Castiel started and then looked at Sam for his approval.

With both of them looking in his direction, Sam hesitated for half a second before realizing he didn't really have a choice. "Yeah. Of course you can come Cas."

Dean then started to ramble excitedly about being the one to teach Cas how to shoot a gun and all that.

Sam suddenly lost his appetite for the last half of his burger. What was the big deal? Cas coming along shouldn't even be a surprise anymore. You'd think he'd be used to it by now.

Late that night Cas went home (which coincidentally was just a few floors above them) and promised to be back early morning.

Cas was pretty much on his own mostly. No parents around the house just like the two brothers. He had some siblings but they just popped in every once in a while. In a way, it was obvious how perfect Dean and Castiel were for each other. Who would ever try to get in the way of that?

After the front door closed and locked, Dean took a seat on the couch next to Sam who has been aimlessly channel surfing for the past hour.

"Hey, Sammy. What'cha watching?"

"Nothing good's on," Sam stated more dryly than he intended.

"What's eating at you? I can tell something's up." This has been true for as long as Sam could remember. Dean was the one who knew what would stop Sam from crying when he was an infant. Even their own dad didn't get that right most of the time.

"Nothing. I.. I'm just nervous about meeting up with Jessica tomorrow afternoon." That wasn't it. But it easily could have been.

"Ah don't worry about that, tiger. You'll do fine. You just gotta relax. Think about it this way, she's in your last period right? Where you sit in the back and ace the class while half asleep?"

"Yeah so?"

"Well she's the one who came up to you, right?"

"Dean how is this going to help?"

"Just hear me out, little brother. Well technically, you got her interested in you while half asleep! Imagine how much she'll like you when you actually put in the effort. Trust me, she'll like you even if you showed up in a clown suit."

"Sometimes I think you really believe that I'm a mini version of you, Dean. And no. You know I hate clowns. Don't even joke about it." Sam shuttered just at the mention of clowns.

"Sorry. Forgot. But about Jess, just don't sweat it. Kick back, order food, make fun of the waiters, you'll do great." Dean patted his little brother on the shoulder as a comforting gesture.

"Thanks Dean." Sam smiled and he actually did feel a little better.

— — — — — — — — —

6:00am. Sam woke up fifteen minutes before his alarm clock. He honestly tried to sleep but he was too excited to have any success. He hopped out of bed and instantly started lacing up his shoes and then turned his attention to the guns. He was wiping down his favorite pistol when Dean knocked on his door and came in with a duffle bag in his hand.

"Hey Sammy. You ready? Dressed?"

"I've been dressed, Dean." It was true. Sam chose to sleep in his hunting jacket despite the rough and uncomfortable exterior.

"Alright. Guns ready to go?"

"Just finished wiping down the last one," Sam gleamed as he put the guns inside Dean's duffle bag to be loaded in the trunk. "When are we gonna head out?" Sam reminded Dean of a little toddler asking to go to the candy store.

"In a minute. I'll call up Cas and see where he's at. You still need to brush your teeth and comb that hair. Have you looked in a mirror yet, bro?" With that, Dean left the room.

The silver phone flipped out of Dean's pocket and was just about to be dialed. As if on cue, there was a knock on the door just before Dean hit the green button.

Castiel was standing in the doorway in a trench coat and black jeans and laced shoes.

Dean opened the door and couldn't help but crack a smile. There wasn't any particular reason, he was just happy. Happy that he was going shooting with Sam. Happy that his boyfriend was gonna be there. Happy that he was gonna make glass explode. Just plainly happy.

Dean grasped Castiel's hands firmly and pulled him into the apartment, towards himself.

"Hey, babe." Dean's voice was warm and enticing. He pulled Cas a little closer and went in for a kiss. Castiel gladly responded with a peck on his soft, moist lips.

"Good morning to you too," replied the shorter one. "You seem to be in a good mood. I like it."

"I just know it's going to be a good day." Dean stole one more peck on the lips before he let Castiel's hands go and walked over to the fridge. "Do you want anything to drink? Coffee? Juice? Beer? Sam and I were talking about going to the diner when we finish with the guns."

Castiel leaned his elbows on the counter and rested his chin in his palms. "I'm fine, Dean. Thanks. About the guns.." he started.

"Yeah, it's gonna be great. You ready?"

"If by ready you mean nervous then yes." The pair of blue eyes shifted from Dean's face down to the wooden floorboards.

"Nervous? What for? They're just guns. You'll do fine." Sometimes Dean forgets that not everyone grew up in a childhood with daggers and rifles as Christmas presents.

"Dean, I've never even held a gun before." He still couldn't meet his boyfriend's eyes.

Dean stepped so that he was leaning back on the counter and pulled Cas towards him like he did before. His hands wrapped around the waist of the trench coat and he tugged Cas closer and closer to him. Soon enough, their chests were just a few centimeters apart. Dean took his finger and lifted Castiel's chin so that their eyes locked on one another's.

"Hey, you have no reason to be nervous. Wanna know why?"

"Why?"

"Because you're gonna have an awesome teacher that will be there every step of the way," said Dean in a soothing and confident tone. He followed the statement with one of his famous winks.

Castiel's lip curled into a half smile. He lifted his arms and gently placed his hands on Dean's leather shoulders, pulling him a little closer which covered the remaining space between their upper bodies.

"Well then," whispered Cas, "lucky me." In a fraction of a second their lips were once again pressed together, as if they had both simultaneously given into their greatest temptation. This kiss was longer than the two before. Longer, harder, better. They're mouths wrestled and seemed to play a game of tug-o-war. The tenderness of their lips touching was magnified by the increasing desire and greed for each other's taste.

Minutes passed but it seemed like seconds. In those moments, those perfect moments, Dean couldn't ask for anything more. His hands around Cas' waist, pulling him closer. Castiel's fingers intertwined around his neck, pulling him deeper into the kiss. Dean wished this moment could last longer. Maybe forever. Everything was just so right. Time ticked by and both of them forgot every worry or care they had in the world. Almost nothing else mattered because they were there, entangled with each other, and everything was perfect. Everything else around them melted away and they focused on nothing but the feeling of the other person's lips on their own.

They might have stayed that way for hours, if it weren't for a sudden vibration in Dean's pocket.

They're lips finally parted long enough for a decent breathe of air. Dean tried his best at not sounding petulant.

"Hello?"

"Dean, where are you two? I've been in the car for over ten minutes now!" Sam must have slipped past them and out the front door while they were.. occupied.

"We'll be there in two seconds, Sammy."

The two boys looked into each other's eyes and grinned as if to say "we'll get back to this later."

After one final check, the two boys left the apartment and locked it behind them.


	3. Chapter 3

The early morning was cloudy and a little chilling, but that was just the way the boys liked it. The field was wet with dew and most of the birds haven't woken up yet. It was late March and it was said that the temperatures would be rising soon, but for now the sun was tucked away under a blanket of clouds and the cool air had an assuaging effect on the atmosphere.

Sam was fidgeting in the front seat. If it weren't for the seatbelt, he might have jumped with excitement. He stared out the window as the fence posts flew behind them. He was too distracted to even listen to what Dean and Cas were talking about. When they pulled into the parking lot of the open grass area, Sam bolted out of the door and had the trunk open before either of the others could unbuckle their seatbelts.

Sam eagerly swung the heavy and too big duffle bag over his shoulder and it hit his back with a thud. Sam was known for being skinny and kind of small (but he was growing! He checked!), but he constantly impressed others with how much weight he could take on. The fourteen year old with the thirty plus pound bag on his back was attempting to grab the two wooden crates when the other two emerged around the back of the car.

"Why don't you take the bag and start prepping, Sammy. We got these. We'll meet you out there," Dean suggested as he lifted one of the crates.

Sam nodded obediently and made a steady jog over to the middle of the field. The bag dropped off his shoulder and he started inspecting each of the guns. As his hands moved over the weapons almost subconsciously, his mind began to wander to all the memories he and Dean shared in this field.

Dean started coming out to the field for target practice with their dad at age ten. He may not have taught the boys how to multiply or how volcanoes erupted, but he passed every ounce of knowledge he had about guns to his eldest son. They would head out in the early mornings when Sam was still in bed and came back around lunch time. At first Dean seemed to be enjoying himself. Any quality time he had with his father was cherished. But after a few months, the guns stopped being much fun. As a former military man, John thought of the guns as preparing Dean to follow in his footsteps to war. Quality father-son time turned into rigorous trainings. Sam noticed the two of them coming back later and later in the afternoon. Turns out John would make Dean hit at least fifty bottles. For every miss, he would chug down the bottle he was drinking and add it on to the fifty. Dean prayed to God that he wouldn't miss anymore. The more he missed, the more Dad drank. And the more he drank, the more furious he would be with his son.

"I'm not gonna let you waste my bullets, boy!" he would yell. Soon enough, Dean could hit fifty bottles in a row. His reward was nothing more than a stern, "finally."

A few years passed and one rainy day when Dean was twelve, he told his Dad that he didn't want to join the army. He didn't want to leave Sam alone and that he felt bad enough leaving his brother alone in the apartment for hours. This sparked a bomb in John's head and one of the most intense fights between the two of them. Sam mostly remembered Dean hiding away with him in his locked room and then tossing at least a dozen empty beer bottles in the crates the following morning. Come to think of it, that was the first time Sam really saw his brother stand up to his Dad. The fact that Dean didn't want to join the army was ironic to Sam, because he always saw his brother as Dad's perfect soldier. The perfect soldier that he could never be.

"Dad's just stressed out from work," Dean would tell him. Even after everything their father has done to him, Dean never blamed his father on his character alone. This was one thing that Sam could never understand about Dean.

The guns were locked away and collected dust for years. Dean didn't go out to the field and Sam didn't wake up to an empty apartment anymore. The entire subject was swept under the rug and there was an unspoken rule to not bring it up.

Sam's first time out in the field was years later with Dean. It was quite a random surprise when Dean entered his room and asked invitingly, "Hey Sammy, wanna go out and shoot a few targets?" Sam agreed and from that day on, the guns weren't a dangerous topic anymore. The field transformed from the former boot camp that Dean knew it to be to a warm sanctum where the brothers laughed and grew closer to one another. It was where it was always just the two of them. In the middle of that field is where Dean taught Sam the different kinds of guns and how to load each of them. Dean taught him everything from how to hold the gun, how to aim, to how to wipe it down to keep from scratches and rusting.

Not once did either of them yell at each other. Not once did Dean say a bullet was wasted when Sam missed. The older brother would just stretch his arms around the smaller boys shoulders and cup his hands around the pair of smaller hands, one on the barrel and the other on the trigger, and guide the gun to the center of the bottle. It was protective and encouraging. Sam never forgot the feeling of shooting that first gun with Dean right at his side.

"Alright. Now.. fire," Dean would say low and firmly, as if being too loud would scare away the target.

Sam flexed his index finger and pulled the trigger. There was a loud shot from the gun followed by the sound of breaking glass. Sam's eyes widened and his jaw dropped. He then turned to face his brother with beaming eyes and a wide smile.

"Did you see that?!" Sam remembered saying to Dean.

Dean nodded and smiled back at his overjoyed brother. "Alright, now let's see you shoot one down on your own. You can handle this one easy."

Sam snapped back into consciousness and was back on the field prepping the guns with the biting air rushing through his hair. He turned his head towards the impala and saw Dean followed by Castiel about ten feet away with the crates of empty bottles.

"You ready?" Dean called to Sam over the sound of the breeze.

"Of course I am!"

The crates were set on the grass about twenty five yards away with the open end down. The empty bottles cluttered the area around the two boxes and four of them were positioned an equal distance apart from each other on top of the flat surface.

"Alright Sammy, hand me the shotgun. Let's warm these babies up. They haven't been used in a while." Dean smirked as Sam handed him the gun. The two boys stepped back from the man with the weapon as he pumped the forend and took aim at the leftmost bottle. He inhaled the cool air through his nose and focused his emerald eyes on his target. Then as if a green flag waved in his head, Dean shot not one but four bullets consecutively. When they squinted to look for the bottles on the crates, all they saw was an empty surface except for a few shards of fragmented glass. Dean looked back at the two staring in awe at his show. "This baby's warmed up," he said coolly.

Warmed up? Sam knew that that was not to warm up the gun. That was definitely showing off for his boyfriend. And judging by the agape expression on Cas' face, it worked and Dean noticed it too.

"Alright Dean, my turn. You go set up four more bottles while I reload the gun." With one final wink in Castiel's direction, the overconfident showoff did as his little brother said.

When he returned, Sam was already taking aim and waiting for Dean's okay. Dean did a light jog the last three yards of the way between him and Cas and swung his arm around the boy in the trench coat's shoulder. "Alright Sam. Shooting one of four. Ready? Aim. Fire."

The shot echoed through the open air and was greeted half a second later by the chime of broken glass.

"Woo! Nice shot, Sammy!" Dean cheered as he fist pumped the air with his free hand, "Alright. Two for two. Ready? Aim. Fire!"

Once again, the loud bang from the gun followed by the shattering of glass filled the silence and seemed to expand to reach all ends of the field.

"I thought you'd be at least a little out of practice, bro. What, you been sneaking over hear at night or something?" Dean joked which made Sam's face light up even more.

"Nope. Just learned from the best," Sam replied proudly.

The next two shots were fired with the same repetition. Sam was ecstatic and reacted as if he just won the lottery.

"YESS! Four for four, Dean! I'm so gonna beat you this Christmas!" Sam cheered as he went to go reload the gun.

Dean was chuckling and Castiel was just watching him, captivated by his perfect features. "You know he worships you right?" says Castiel as the couple stares at Sam with the guns.

"Worships? You make it sound like I'm a king or something. Nah.. All kids look up to their older brother," states Dean modestly. If Dean was the king of anything, he would be the King of Modesty.

"No, you two are different. I look up to my brothers like any younger sibling would. Sam.. To Sam, you really are everything to him." Castiel can see the complex emotions building up behind Dean's stolid expression. "I've never seen a relationship closer than you and his. It's admirable. Inspiring even," Castiel continued.

Dean let Cas' words sink in and stared closer at Sam loading the pistols, exactly the way he showed him on their first day out here. Dean thought about how up until recently, Sam was his whole world. He stood up to his dad for Sammy. He decided to finish high school instead of getting a full time job at Bobby's garage so that he would be able to watch out for Sammy. He remembered how he could barely look himself in the mirror when he came home from the field one late afternoon and saw Sam's hand wrapped in bandages because he burned himself trying to cook eggs and bacon. For the majority of his life, Sam was his everything too.

Until a few months ago, when he met Castiel. Ever since he first laid eyes on the dark haired boy in a tan overcoat, his world changed dramatically. He admired and eventually fell in love with everything about him. Dean would go on and on at the diner to Sam about "this boy's" eyes, hair, voice, and the way he walks, talks, eats, and every minute detail he could think of. After around three months of infatuation, the brothers were in the field for their Christmas competition and that's when Sam decided to shut Dean up by saying, "for the love of God, ask the boy out already, Dean! What are you waiting for? An angel to descend from heaven and give you permission?" And that's how Dean mustered up the courage to ask Castiel on their first date on the first day back from break and a week later it became "official." Dean's utopian world consisted of nothing more than Sam and Castiel. With the two of them around and happy, Dean's world was as good as it gets.

Dean looked over at Cas now, who was still admiring the shape of Dean's lips, and said, "Alright Cas, you're up. Sam, hand him the gun."

Sam just returned from replacing the four beer bottles at the other end of the range and ran over to the duffle to pick up the shotgun and held it out to Castiel. When he refused to take it, he held it out to his brother who gladly accepted it. He then replaced the couple's former spot away from the shooting area to observe.

The pair of crystal blue eyes were wide and worried. "Uh, Dean, I still don't really think-"

"C'mon, babe. Have some confidence. You'll do great!" Dean pumped the gun before placing it in Castiel's hands. "Alright, it's ready to go. Now put one hand here," instructed Dean as he pointed to the barrel, "and the other here," he motioned to the trigger.

"Okay. Like this?" asked the pupil uncertainly.

"Almost. Just a little more.. like.. this." Dean then proceeded to wrap his arms around Castiel's shoulders.

Sam's eyebrows scrunched together at the sight of the familiar gesture.

Dean then cupped his hands over his boyfriend's, just as he did once before. He adjusted his student's hands slightly and helped him aim directly at the paper wrapping around the bottle. "Relax, Cas. Take a breath. Ready?"

"As much as I'll ever be," Castiel replied.

Dean tightened arms around the dark haired one protectively as an act of reassurance.

Sam was grinding his teeth while watching what seemed like a reenactment of his memories, except someone else was playing his part.

Dean's voice was low and firm, just like all those years ago. Sam couldn't hear the words, but he knew exactly what they were.

"Alright. Now.. fire," Dean said in Castiel's ear at the same time as Sam silently mouthed the words to himself.

The gun went off and Dean stood solidly to protect Cas from the recoil. The faint sound of the glass breaking was the sound of success.

"Hey! I hit it!" the shorter one said with a mixture of pure joy and surprise. He placed the gun on the grass and turned to face his teacher. "You're amazing!" Castiel reached up to meet Dean's lips for a quick peck.

Dean smiled at how happy the other boy was. "Don't look at me, you're the one who pulled the trigger. According to the law, you get the credit." The two lovers smiled and blushed at each other for the next few seconds.

Sam was trying to compose his face a couple yards away. Sam slowly made his way to join them and during those few steps he was able to construct his perfectly convincing façade, another skill he learned from his brother.

"Hey nice shot, Cas." He held his hand up for a high five.

"Thanks, Sam," Castiel replied as he clapped Sam's hand with his own, "couldn't have done it without your brother though. I now see how you became so proficient in shooting."

"Yeah. He is great," the younger Winchester stated.

"Stop it guys, seriously. It's not that big a deal," Dean pleaded with a hint of sarcasm. He raised his arm and ran his hand on the back of his neck in an embarrassed attempt to hide the red creeping up. "Okay. Few more rounds, then we hit the diner. I'm starving!"

The three of them stayed out in the field for a few more minutes or so, and throughout the entire morning Sam couldn't get rid of the gut wrenching knot building in his stomach. But of course he wouldn't let anyone know about it. He didn't want to ruin the good mood.

_/This chapter was a bit longer than the first two, but I enjoyed it. But hey! Little Sammy's first date scene is up next! Tell me what you thought! Thanks, darlings. _


	4. Chapter 4

_/Sorry this took a little longer than others. I'm on vacation with family atm. But nevertheless, here you go! I hope you enjoy. These cuties makes me squeal. Review please? Tell me what you think! Thanks, darlings!_

"DEAN! Are you ready to go yet?" Sam called through his open bedroom door. It was 5:00pm and Sam promised that the car would be outside Jessica's door no later than 6:30. When the boys got back from the diner around one in the afternoon, his date took priority over everything else on his mind. Well, except for a miniscule, little weight in his gut that he couldn't shake. But he didn't have time to deal with that right now.

Dean let it slip to Bobby that Sam was going on his first date and he was so excited that he personally reserved a table at his favorite restaurant.

"It's one of the nicer ones, not some old, dingy, twenty year old Denny's. The manager owes me a favor anyways. It'll be perfect," Bobby said over the phone. Sam reluctantly agreed and tried to comfort his mind by telling himself the restaurant will be fine. She'll like it. He hoped.

He tried relaxing with a book while he still had a few hours to kill, but his mind kept constructing every possible way the evening could go horribly wrong. What if he knocked on her door and her dad saw him and didn't let her go? What if he clumsily spilled food on himself at the restaurant? What if.. The list went on endlessly. By the time Sam had to start getting ready, his hands were starting to tremble.

Sam probably could have waited two more hours to get ready and they would still have time to spare, but he wanted to make sure. There is no way he's making Jessica wait. The getting ready process was all done with nerves getting more intense every time he looked at the clock. Shower, blow drying hair, clean and unstained dark pants matched with a light blue buttoned plaid shirt. He even sneaked in a little bit of Dean's cologne when he wasn't watching.

Dean met Sam in the kitchen and motioned to the digital numbers displaying 5:17 on the microwave, "Sam. Will you chill out? We have plenty of time. It only takes fifteen minutes to get to Jessica's and then-"

"Fifteen minutes to Jess' house, then another fifteen to the restaurant. That's assuming we take the freeway. I checked this morning," Sam interrupted, his mouth moving at a hundred miles an hour.

"Yeah, and you checked last night too. And I saw you look it up on your phone on our way home. Sam, you need a beer or something." Dean said lightheartedly, but just received a cold glare in return.

"Shut up, Dean," was all the little brother could muster up. He was fidgeting with his fingers on the kitchen counter like he always does when he's nervous.

Dean's big brother instincts told him that this was when he was supposed to step in with some reassuring words. So he rounded the island and gently pulled Sam off the stool.

"Alright, come here. Let me get a look at you," said Dean as he brushes off the blue, plaid shoulders. "Sam. Your hair. It makes you look like one of those private school prep boys that where sweaters like capes," the older one criticized. His hand instantly went to offer Sam's hair some assistance. After some expected resistance, the shaggy hair was tousled and shaken to Dean's liking. "There. Makes you look a little daring I'd say. Jessica won't be able to resist you." Dean looked at his brother the same way an artist looks at his finished masterpiece.

"I hope you're magic hair trick works on her parents too," Sam groaned as he smoothed down his shirt.

Parents. This was not one of Dean's areas of expertise. He dodged that bullet with Cas, but is still dreading the first holiday that all his older brothers will return for a family reunion. But for Sam, he'll attempt any kind of help he can give. "I don't think you'll have a problem with that. You're smart, got good grades, you're polite, you're what parents want for their daughter. So don't sweat it."

Dean felt accomplished when the kid finally was able to crack a smile. It was all true. Sam didn't have a rotten bone in his body. Dean couldn't help but wish he was as good as Sam was. The idea that Sam was the one who worshipped him blew his mind, because Dean believed Sam was already so much better than he could be.

"Uhm, Dean? I don't mean to be rude but.. are you planning on changing before we leave?" Sam asked with a raised eyebrow.

Dean inspected his ACDC shirt with a small hole at the edge of the left sleeve and his faded jeans with an oil droplet trail on his knee. "What? You're the one with the date, not me."

Sam groaned and rolled his eyes. "Please Dean? Just no rips or stains. Jess is still gonna meet you when she gets in the car and.. look I really like her and I just want.. C'mon Dean, do it for me?" Sam pleaded. He saved that line for the extra important things he needed Dean to do.

Dean lets out an exaggerated sigh and trudges to his room. "Fine. But don't push it Sammy. Or you and your girlfriend are taking a hike back home after dinner," Dean threatened as he pulled out a new shirt and a clean pair of dark jeans.

"No you won't!" called Sam from the kitchen. "I heard Bobby make you promise to drop off and pick us up and not a minute late."

Dean could almost hear his brother smirk. In his opinion, Sam straddles the line between just plain smart and a smart ass. Dean emerges from his room in a dark, solid blue v-neck and black jeans. He does a three sixty for Sam to approve.

"Good now? No stains or rips except for one tiny hole in the crotch. But I don't think Jess will be looking there so I think we're good."

The brothers killed a few more minutes with light hearted jokes and stories of Dean's first "date" which was basically a make out session behind the bleachers with hot cheerleader Anna Milton freshman year. Finally, Sam saw the microwave flash the time 6:05 and Sam jumps to his feet.

"Dean! We gotta go. I don't wanna be late because of traffic," Sam exclaims as he grabs his jacket and opens the front door.

Dean grabs his jacket and the keys and strides out the door and Sam follows nervously but excitedly follows and shuts the door behind him.

The clock in the impala read 6:15 and they were five minutes away from Jess' house. The car has been mostly quiet except for Sam giving directions to which Dean always replied "I know, Sam. I Googled it last night." Sam was rehearsing what he would say when the door opened and he was in front of Jessica's parents. He tried to make Dean believe he was totally cool, but Dean could sense his brother's nerves radiating from the passenger side.

Dean fished in the middle compartment for a small metal tin. "Here, Sammy," he offered. Sam opened the box to find small white tablets. "They're lucky. Go ahead and take one." Dean noticed his brother's wide, apprehensive eyes. "They're breath mints, Sammy!" The look didn't change. "They're clean. Promise. Just take one."

Sam popped one of the tablets into his mouth and tasted the minty flavor making his mouth cold. "Lucky, you say?"

"They haven't let me down yet. Just ask Cas. He loves them."

"Dean, Cas would love you even if your breath smelled like pickle juice and onions." Both of the brothers laughed.

"Shut up," Dean said while chuckling. "So you ready?" They pulled up in front of the address Sam's practically memorized by now and slowed to a stop.

It's 6:27. Sam stared at the dark green front door for at least half a minute without saying a word. He swallows the lump that has built up in his throat and tries to even out his breathing. "Dean?" Sam's voice was small, "I'm still nervous.."

Dean put a comforting hand on his brother's shoulder. "You'll do great. Just be the brilliant Sam Winchester that we all know and love."

Sam cracked a smile and let out a long breath. Okay, it's time to do this. Don't want to keep Jessica waiting. He exited the car and started up the gravel pathway. That lump in his throat started to form again. He rang the doorbell and fiddled with his fingers while waiting for someone to open the door.

A middle aged man with round glasses and a collared shirt came to the door. Sam grabbed a quick breath and spoke clearly and firmly, trying to sound as confident as he could, "Mr. Moore? Good evening, I'm Sam Winchester."

The man inspected Sam in the doorway, from the tips of his hair to his faded shoes. Then he smiled and Sam felt he could breathe again. "Ah. Evening, Sam. Jessica's been telling us about you. Why don't you come in and relax. Honey!" he called to his wife, "Sam's here. Come say hello."

Sam walked into the clean living room and took a seat on a brown, leather couch after introducing himself to Mrs. Moore.

"Jess! Sam's here!" The woman with blonde hair called upstairs. "Sorry to keep you waiting. That girl has tried on at least six different outfits before you got here." This made Sam smile.

"Mom!" Jessica's voice from upstairs was irritated and a little embarrassed.

Sam chuckled and said coolly, "I don't mind waiting. You have a lovely house." The mother thanked him for the compliment. Sam was doing great. This wasn't as bad as he expected. He was actually good at talking to parents. For the next few minutes Mr. and Mrs. Moore asked Sam about school, hobbies, et cetera. Mr. Moore's ears perked up when Sam mentioned his interest in becoming a lawyer.

"Law, huh? That's a great field. I know it's still a long ways away, but have you considered any specific colleges?" The man asked in a kind and easy going tone.

"Well, my brother, Dean, says I should apply to Stanford. But I'm not sure if they'll accept me. They're standards are pretty high." Sam said modestly. Another little trait that Sam subconsciously inherited from his older brother.

"What, intelligent, hardworking boy like you? I think you should go for it. Maybe you'll rub some of that off on Jess," the dad teased.

"Very funny, Dad." Jessica was half way down the stairs wearing a pair of denim jeans, blue blouse with ruffles at the bottom, and wedged heels about one and a half inches tall. Her long, golden hair was curled and there was a touch of sparkly lip gloss on her lips. She entered the living room and smiled when she saw Sam. "What, too casual?"

Sam's attention was enthralled by the sight of Jessica coming down the stairs. It took him a second to process the question. "No, not at all. It looks," he cleared his throat, "you look nice."

The two smiled and Sam started towards the door. "We better get going. Our reservations are in fifteen minutes," Sam said still looking at Jess.

"Where you kids eating?" Asked Jessica's mother.

"Harvelle's Roadhouse. It's my uncle's favorite restaurant and he's friends with the owner," Sam informed. He then held the front door open for his date and walked onto the front porch. He turned back to the parents who were now standing in the doorway. "Thank you for letting Jessica go out tonight, Mr. and Mrs. Moore. We will be back to drop her off tonight."

"Jess, no later than ten, understood?" Mr. Moore informed his daughter.

"Yes, daddy," Jessica replied. Sam thought her voice sounded like wind chimes.

Mr. Moore then caught sight of the impala waiting in front of the house. "That your brother?" Sam nodded. "Nice car. Tell him to drive safely."

"I will, Sir. You don't have to worry, my brother won't let anything happen to us," Sam said with admiration in his voice. It was true. He didn't feel safer anywhere but with Dean.

Jessica kissed her parents on the cheek and waved one final goodbye before walking next to Sam, who opened her door for her before going around to the other side to let himself in.

Dean smiled as he looked at the kids in the rearview mirror. "You guys coordinate your first date outfits over the phone or something?"

Sam and Jess looked from their own shirt to the other and just started laughing.

"Apparently we did," laughed Jessica.

"By the way, I'm Dean. Sam's older brother. You don't have to introduce yourself. You're the famous Jessica Moore." Dean put on one of his half smiles.

"Dean!" Sam's voice was one of disbelief.

Jessica just smiled at the boy sitting next to her. "Nice to finally meet you, Dean. Sam talks a lot about you. And famous? Hope Sam hasn't told you anything too bad."

"No nothing too bad. He just told me about you stole a car a few years back and ran from the cops." Dean laughed to ensure the girl that he was kidding, but evidently he didn't have to.

"Dammit Sam! I told you those records were expunged!" Jessica played along with Dean's joke and made the two Winchesters laugh at her quick response.

"I like her, Sammy," Dean said looking in the mirror at the back row.

The younger brother looked from Dean to Jessica. "Same here, Dean." Jessica smiled and blushed a little. Dean gave his brother a 'smooth move' look in the mirror.

The impala pulled up to the roadhouse and slowed to a stop in front of the entrance.

"Alright, you kids have fun. Just send me a text and I'll come get you guys. And anything from the bar is off limits, Sammy," Dean commented.

"Right, Dean. Because that's totally something I would do," Sam retorted sarcastically. "Okay, I'll text you. See ya later!" And with that, the impala revved and left the excited and nervous fourteen year olds at the restaurant.

"Reservation for Winchester?" Sam said when he got to the front desk. A slight smirk grew on his face, thinking he sounded very mature for having a reservation. Jo recognized Sam as soon as he walked through the door and easily picked up on his trying-to-be-cool tone.

"Ah yes. Mr. Winchester. Table for two. Will you be needing any kid's menus?" Jo asked playfully trying to embarrass the little boy, who she's known since he was in diapers, on his first date.

"Jo!" Sam complained. "Jess, I swear not all of my family and family-friends are like this." Sam looked back at his date as Jo led them to their booth by a window.

"I think they're great, Sam. Hilarious, I might add. You're the only one not laughing," Jessica said with a sincere smile as they sat down on the leather padded seats.

Jo let out an amused giggle as she set down menus. "I like you, Jess. We could be great friends. You fit right in with Sam's crowd."

Dinner started out without Sam embarrassing himself any further than Dean and Jo already have. The two ordered a couple burgers and soda with a plate of fries in the middle to share. Sam thought everything was going well. They talked about anything that came to mind. School, movies, embarrassing stories about Sam's family members, and much more. The conversation was effortless and natural. All the nervous jitters melted away and the two teens just enjoyed each other's company.

Everything was perfect.. Until Sam's long arm knocked over his sprite. _Shit shit shit.._ The clear liquid started running off the other end of the table and threatened to land on Jessica's jeans. She quickly dodged towards the inner part of the booth and let the soda drip onto the spot she was formerly sitting.

"I'm so so sorry," Sam started with a flustered tone. He grabbed a couple napkins and started wiping up his spilled drink on the tabletop and then walked around to clean the seat.

Jessica watched Sam frantically clean up the mess as he repeatedly apologized. She didn't respond until he sat back down in his seat looking a couple shades of red. "It's okay, Sam. I'm fine, see? Not a drop." Sam started to relax at the sight of Jessica's smile. She reached for a few fries and after putting one in her mouth she threw the other and it bounced off Sam's cheek.

"Hey!" Sam said in surprise at the airborne fry.

"That's for almost making it look I peed my pants," Jessica said jokingly upset.

Sam smiled wide and stared at her for a few seconds before deciding to grab a fry to retaliate. Jessica gasped as it landed in her hair and the two of them started to break out into laughter. A few more shots were fired before Jo walked by and gave their table a stink eye. And they bit their lip to suppress their remaining giggles.

When the kids were finally able to catch their breath, Jessica put an elbow on the table and rested her chin on her palm looking across the table curiously. "So, tell me Sam, if I ask you something will you answer completely honestly?"

"Yeah, of course. What is it?"

"When you first saw me in geometry what was your first impression. And I want honest. Don't just be nice to make me feel good." She stared at Sam's face as his mind went back to the beginning of the school year.

Sam remembered the first week of school and always staring at the clock for his last class to finish. Jessica sat in the row to his right and four seats in front of him. He noticed her long, blonde hair from day one. It reminded him of the picture he had of his mom in his wallet. Sam really started to notice her when she would raise her hand with the right answers every time. She impressed him. Brilliant really. So brilliant and beautiful that he had never thought a girl like Jessica Moore would notice the kid with matted hair in the back row.

"It probably took about a week for me to know I had a crush on you. By then I knew you were pretty, smart, funny, and more. But..," he stirred the remaining ice in his glass with his straw as he hesitated, "but I honestly never would have really done anything about it. I was so surprised when you called me over at the end of class yesterday." His looked innocent and vulnerable for a few seconds. He finally met Jessica's eyes to see her expression.

Jessica had a surprised look on her face, "a week? Why didn't you say anything?" She said it as if it was as easy as asking someone to pick up your pencil.

"Well," he broke eye contact once again, "I have to answer honestly right?" Jess nodded. "Well I just never thought you would have even looked in my direction," Sam admitted sheepishly. "I mean, look at you! You're Jessica Moore. Who doesn't adore you?"

Jessica blushed but quickly rebounded. "Yeah and you're Sam Winchester! What makes you think I wouldn't have noticed you?"

"If you haven't noticed, I'm not exactly the coolest guy around campus.." His voice let the sentence hang. _Not like Dean_ Sam's thoughts finished.

"Well I think you're pretty great, Sam. You're smart, funny, you were a hit with my parents, and that's highly impressive, you drive around with your brother in his cool car, Sam to me you're pretty brilliant," Jessica said in awe. She bit her lip, a little nervous. She wondered if she sounded like a complete idiot. Sam just smiled at her and prayed he wasn't blushing too noticeably.

"Thanks Jess." The two smiled at each other.

The rest of their date followed the same course. They discovered trivial things about each other. Favorite colors, pet peeves, childhood stories, and the list went on. They talked endlessly until most of the other dinner customers have gone, save for a few bar hoppers. They didn't even notice the surrounding booths starting to be wiped down for the night.

Sam looked down at his wrist watch and gasped at the time. It was 9:15. Neither of them would have thought they've spent over two whole hours talking about nothing and everything. "Woah, it's late. Jess, you gotta get home soon. I'd like to stay on your dad's good side for as long as I can," said Sam said with a grin. But he knew that he had to give Dean fifteen minutes leeway to get to the roadhouse.

"Ugh. You're right, unfortunately." She sounded sincerely displeased that they didn't have more time together.

Sam paid for dinner and then took out his phone to text Dean.

**Hey Dean. We lost track of time. Could you come get us? Jess has to be back by 10. **

The two of them then decided to sit on a bench out in front of the restaurant under the night sky. Sam wrapped his jacket around Jess and they sat there for a few minutes hand in hand. Although Sam wouldn't have minded that moment to last for hours, he was worried that he wouldn't get Jessica home in time. He nervously checked his phone for Dean's reply.

**No New Messages**

Sam tried again in five minutes.

**Dean? Did you get my last message? I really don't want Jess to be late. We're out front. Text me back.**

Sam continued to check the phone but saw the same disappointing empty inbox every time. He started to worry. Dean always replied to Sam's text messages. Why would Dean not have his phone on him?

Two more messages were sent in the next fifteen minutes.

**Dean. Where are you? **

**Seriously Dean. Did something happen? What's going on? **

They sat out on the bench for a good thirty minutes before Sam felt a vibration in his pocket. It was now 9:35.

**Be there in 5. **

Sam stared at the short message in confusion. His brother was never late picking him up at anything for as long as he could remember. He tried to relax for Jessica's sake but he couldn't shake the thought of _what could Dean be too busy with to not check his phone? _The answer wasn't prominent in Sam's mind but on some level of his subconscious he knew exactly where his brother was and what he was doing.

_/ Next chapter we'll figure out exactly where Dean went after dropping his brother and date off and if Jess gets home in time. But let's hope so for Sammy's sake. Thanks for reading! Again, tell me what you thought. I love hearing your guys' opinions. _


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